N-[2-(3,4-dimethoxyphenyl)ethyl]-4-methoxybenzamide

Base Information

• Chemical Name: N-[2-(3,4-dimethoxyphenyl)ethyl]-4-methoxybenzamide
• CAS No.: 15547-66-7
• Molecular Formula: C18H21NO4
• Molecular Weight: 315.369
• Mol file: 15547-66-7.mol

Synonyms:4-Pyridinesulfonamide, N-cyclopropyl;

Chemical Property of N-[2-(3,4-dimethoxyphenyl)ethyl]-4-methoxybenzamide

Chemical Property:

• Melting Point: 127-129 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• Boiling Point: 505.8±50.0 °C(Predicted)
• PKA: 14.68±0.46(Predicted)
• PSA: 0.00000
• Density: 1.130±0.06 g/cm3(Predicted)
• LogP: 0.00000

Purity/Quality:

N-(2-(3,4-DIMETHOXY-PHENYL)-ETHYL)-4-METHOXY-BENZAMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[2-(3,4-dimethoxyphenyl)ethyl]-4-methoxybenzamide

There total 7 articles about N-[2-(3,4-dimethoxyphenyl)ethyl]-4-methoxybenzamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

4-methoxy-benzoyl chloride (100-07-2) + 2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → N-(2-<3,4-dimethoxyphenyl>-ethyl)-p-methoxybenzamide (15547-66-7)

Guidance literature:

With potassium carbonate; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ol9017529

Reference yield: 80.0%

4-methoxyphenylacetamide (3424-93-9) + 2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → N-(2-<3,4-dimethoxyphenyl>-ethyl)-p-methoxybenzamide (15547-66-7)

Guidance literature:

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol402201c

Reference yield: 62.0%

4-Methoxybenzenethiol (696-63-9) + carbon monoxide (201230-82-2) + 2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → N-(2-<3,4-dimethoxyphenyl>-ethyl)-p-methoxybenzamide (15547-66-7)

Guidance literature:

With dicobalt octacarbonyl; In toluene; at 220 ℃; for 1h; under 11251.1 Torr; Inert atmosphere;

DOI:10.1039/d1ra04736a

upstream raw materials:

4-methoxy-benzoyl chloride

2-(3,4-dimethoxyphenyl)-ethylamine

3,4-dimethoxynitrostyrene

3,4-dimethoxy-benzaldehyde

Downstream raw materials:

6,7-dimethoxy-1-(4-methoxy-phenyl)-isoquinoline

(±)-6,7-dimethoxy-1-(4-methoxyphenyl)-N-methyl-1,2,3,4-tetrahydroisoquinoline

(+)-6,7-dimethoxy-1-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline

6,7-dimethoxy-1-<(para-methoxy)phenyl>-3,4-dihydroisoquinoline

Refernces

• 1、 Barrios-Rivera, Jonathan,Xu, Yingjian,Wills, Martin. "Asymmetric Transfer Hydrogenation of Unhindered and Non-Electron-Rich 1-Aryl Dihydroisoquinolines with High Enantioselectivity". supporting information. p. 6283 - 6287. Retrieved 2020/09/02.
• 2、 Perez, Marc,Wu, Zi,Scalone, Michelangelo,Ayad, Tahar,Ratovelomanana-Vidal, Virginie. "Enantioselective Synthesis of 1-Aryl-Substituted Tetrahydroisoquinolines Through Ru-Catalyzed Asymmetric Transfer Hydrogenation". . p. 6503 - 6514. Retrieved 2015/10/19.